Photocatalyzed Direct α-Alkylation of Esters Using Styrenes

Pengzhi Wang; Anna V. Bay; Emelia J. Farnam; Karl A. Scheidt

doi:10.1002/adsc.202300253

Photocatalyzed Direct α-Alkylation of Esters Using Styrenes

Pengzhi Wang, Anna V. Bay, Emelia J. Farnam, Karl A. Scheidt^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

A mild photocatalyzed approach to achieve the α-alkylation of esters via formation of an α -radical is disclosed here. Cesium enolates of esters were generated in situ using Cs₂CO₃ as a base. A subsequent photocatalyzed oxidation at the α-carbon of these enolates produced an α-radical that was added into activated alkenes. This is the first example accessing the α-carbon radical of esters in photoredox catalyed transformations.

Original language	English (US)
Pages (from-to)	2361-2366
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	365
Issue number	14
DOIs	https://doi.org/10.1002/adsc.202300253
State	Published - Jul 18 2023

Keywords

Carbonyl compounds
Cesium enolates
Photoredox catalysis
α-Alkylation
α-Radical

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.202300253

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title = "Photocatalyzed Direct α-Alkylation of Esters Using Styrenes",

abstract = "A mild photocatalyzed approach to achieve the α-alkylation of esters via formation of an α -radical is disclosed here. Cesium enolates of esters were generated in situ using Cs2CO3 as a base. A subsequent photocatalyzed oxidation at the α-carbon of these enolates produced an α-radical that was added into activated alkenes. This is the first example accessing the α-carbon radical of esters in photoredox catalyed transformations.",

keywords = "Carbonyl compounds, Cesium enolates, Photoredox catalysis, α-Alkylation, α-Radical",

author = "Pengzhi Wang and Bay, {Anna V.} and Farnam, {Emelia J.} and Scheidt, {Karl A.}",

note = "Funding Information: We thank Northwestern University and the National Institute of General Medical Sciences (R35 GM136440) for support of this work. The authors thank Dr. Qiupeng Peng (NU) for assistance with HRMS and Dr. Jing Cao (NU) for assistance with F NMR. 19 Publisher Copyright: {\textcopyright} 2023 Wiley-VCH GmbH.",

year = "2023",

month = jul,

day = "18",

doi = "10.1002/adsc.202300253",

language = "English (US)",

volume = "365",

pages = "2361--2366",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

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TY - JOUR

T1 - Photocatalyzed Direct α-Alkylation of Esters Using Styrenes

AU - Wang, Pengzhi

AU - Bay, Anna V.

AU - Farnam, Emelia J.

AU - Scheidt, Karl A.

N1 - Funding Information: We thank Northwestern University and the National Institute of General Medical Sciences (R35 GM136440) for support of this work. The authors thank Dr. Qiupeng Peng (NU) for assistance with HRMS and Dr. Jing Cao (NU) for assistance with F NMR. 19 Publisher Copyright: © 2023 Wiley-VCH GmbH.

PY - 2023/7/18

Y1 - 2023/7/18

N2 - A mild photocatalyzed approach to achieve the α-alkylation of esters via formation of an α -radical is disclosed here. Cesium enolates of esters were generated in situ using Cs2CO3 as a base. A subsequent photocatalyzed oxidation at the α-carbon of these enolates produced an α-radical that was added into activated alkenes. This is the first example accessing the α-carbon radical of esters in photoredox catalyed transformations.

AB - A mild photocatalyzed approach to achieve the α-alkylation of esters via formation of an α -radical is disclosed here. Cesium enolates of esters were generated in situ using Cs2CO3 as a base. A subsequent photocatalyzed oxidation at the α-carbon of these enolates produced an α-radical that was added into activated alkenes. This is the first example accessing the α-carbon radical of esters in photoredox catalyed transformations.

KW - Carbonyl compounds

KW - Cesium enolates

KW - Photoredox catalysis

KW - α-Alkylation

KW - α-Radical

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DO - 10.1002/adsc.202300253

M3 - Article

AN - SCOPUS:85164962079

SN - 1615-4150

VL - 365

SP - 2361

EP - 2366

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 14

ER -

Photocatalyzed Direct α-Alkylation of Esters Using Styrenes

Abstract

Keywords

ASJC Scopus subject areas

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